EP0037526A1 - Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide - Google Patents

Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide Download PDF

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Publication number
EP0037526A1
EP0037526A1 EP81102280A EP81102280A EP0037526A1 EP 0037526 A1 EP0037526 A1 EP 0037526A1 EP 81102280 A EP81102280 A EP 81102280A EP 81102280 A EP81102280 A EP 81102280A EP 0037526 A1 EP0037526 A1 EP 0037526A1
Authority
EP
European Patent Office
Prior art keywords
substituted
formula
preparation
acetanilides
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP81102280A
Other languages
German (de)
English (en)
French (fr)
Inventor
Shinpei Kuyama
Masahiro Aya
Junichi Saito
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience KK
Original Assignee
Nihon Tokushu Noyaku Seizo KK
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nihon Tokushu Noyaku Seizo KK filed Critical Nihon Tokushu Noyaku Seizo KK
Publication of EP0037526A1 publication Critical patent/EP0037526A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Definitions

  • the invention relates to certain new substituted acetanilides, a process for their preparation and their use as herbicides.
  • Japanese Laid-Open Specification 154762/1979 states that substituted carboxamides of the general formula in which n stands for 1, 2, 3 or 4, each R individually represents hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, nitro, cyano or alkoxycarbonyl or two R together represent methylenedioxy, dichloromethylenedioxy or difluoromethylenedioxy, R 1 represents hydrogen or alkyl, R 2 and R 3 may be the same or different and each represent hydrogen, alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl, aryl or an optionally substituted heterocyclic group or, together with the nitrogen atom to which they are attached, a substituted or unsubstituted one, optionally partially unsaturated form a monocyclic or bicyclic group which may contain one or more
  • the invention relates to new substituted acetanilides of the general formula in which X is an oxygen or sulfur atom and R is an ethyl, n-propyl or isopropyl radical.
  • the invention further comprises the preparation of substituted acetanilide compounds of the formula (I) by a process which is characterized in that a 2-halobenzazole of the general formula in which X has the meaning given above and Hal is a halogen atom, with a compound of the general formula in which R has the meaning already mentioned and M is a hydrogen atom or alkali metal atom.
  • substituted acetanilides of the above formula (I) are generally included in the above formula (IV), there is no description of the compounds according to the invention in the above-mentioned Japanese patent application.
  • the substituted acetanilides of the formula (I) have a surprisingly superior herbicidal activity compared to known analogous compounds.
  • the compounds according to the invention have a herbicidal activity which is particularly good in terms of specificity compared to the analog compounds described in the aforementioned Japanese patent application.
  • Examples of the 2-halobenzazoles of the formula (II) used as starting materials are 2-chlorobenzothiazole, 2-chlorobenzoxazole and their corresponding 2-bromo compounds.
  • Examples of the compounds of the formula (III) which are also used as starting materials are N-ethyl-hydroxyacetanilide, N-propyl-hydroxyacetanilide, N-isopropylhydroxyacetanilide and their alkali metal salts.
  • the process according to the invention is preferably carried out in the presence of a solvent or diluent.
  • a solvent or diluent any inert L ösungs- or diluents may be used.
  • solvents and diluents are water, aliphatic, alicyclic and aromatic hydrocarbons (which can optionally be chlorinated), for example hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, Methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichlorethylene or chlorobenzene, ethers, for example D iäthyläther, methyl ethyl ether, diisopropyl ether, D ibutyläther, propylene oxide, .Dioxan or tetrahydrofuran, ketones such as acetone, methyl ethyl
  • the process according to the invention can be carried out in the presence of an acid-binding agent, especially when M in the formula (III) is hydrogen.
  • acid-binding compounds are the commonly used agents, e.g. the hydroxides, carbonates, bicarbonates and alcoholates of alkali metals and tertiary amines, e.g. Triethylamine, diethylaniline or pyridine.
  • the method according to the invention can be carried out over a wide range of temperatures. In general, it is carried out at a temperature between -20 ° C. and the boiling point of the reaction mixture, preferably between 0 ° C. and 100 ° C. Normal pressure is preferably used as the reaction pressure, but, if this is expedient, it is also possible to work at elevated or reduced pressure.
  • the compounds according to the invention have only a low toxicity for warm-blooded animals and good selectivity with regard to the crops grown, ie do not show any phytotoxicity at the concentrations which are usually used, they can be used advantageously as herbicides for weed control. "Weeds" in the broadest sense are plants that grow in places where they are not wanted.
  • the compounds according to the invention are excellent in their safety, show superior herbicidal activity and have a wide herbicidal spectrum.
  • the active compounds according to the invention can be used, for example, to control the following plants: dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea , Polygonum, Sesbania, Ambrosia, Sirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, D atura, Viola, Galeopsis, Papaver, Centaurea and Solanum, and Monokotyledon weeds of the genus Setariachlo Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria
  • the compounds for total weed control for example Industrial sites and railway bodies and on paths and squares with or without trees.
  • the compounds for controlling weeds in perennial cultures for example afforestations, decorative tree plantings, orchards, vineyards and gardens, citrus woods, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, W calibrating fruit plantations and hopfields can be and are used for selective weed control in annual cultures .
  • the compounds according to the invention have a superior selective control action, particularly when used as pre-emergence herbicides and as a plant and soil treatment agent for rice field weeds.
  • they show herbicidal activity against the following rice field weeds without having any phytotoxicity against rice plants: the dicotyledon weeds Rotala indica Koehne, Lindernia procumbens Philcox, Ludwigia prostrata Roxburgh, Potamogeton distinctus A.
  • the active ingredients can be used in conventional preparations, e.g. Solutions, emulsions, suspensions, powders, foam granules, natural and synthetic materials, which are impregnated with the active ingredients, and very fine capsules are converted into polymeric substances.
  • preparations can be prepared in a known manner, for example by mixing the active substances with extenders, ie liquid or solid diluents or carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid or solid diluents or carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid diluents or carriers especially as solvents, mainly aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, e.g. Chlorobenzenes, chloroethylene or methylene chloride, aliphatic or alicyclic hydrocarbons e.g. Cyclohexane or paraffins, e.g. Mineral oil fractions, alcohols, e.g. Butanol or glycol, as well as their ethers and esters, ketones, e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, for example, dimethylformamide and dimethyl sulfoxide, and water.
  • aromatic hydrocarbons e.g. Xylene, toluene or alkylnaphthalenes
  • Natural earth minerals for example kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic earth minerals, for example highly disperse silica, aluminum oxide and silicates, can be used as solid carriers.
  • solid carriers for granules there may be crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and - dolomite, and synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, are used .
  • Nonionic and anionic emulsifiers for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and products of the hydrolysis of albumin, can be used as emulsifiers and / or foaming agents will.
  • suitable dispersants are lignin sulfite liquor and methylcellulose.
  • Adhesives e.g. Carboxymethyl cellulose and natural and synthetic polymers in the form of powder, granules or latices, e.g. Gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the preparations.
  • coloring substances e.g. inorganic pigments, e.g. Iron oxide, titanium oxide and Prussian blue
  • organic dyes e.g. Alizarin dyes, azo dyes or metal phthalocyanine dyes
  • trace nutrients e.g. Use salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the preparations generally contain 0.001 to 100%, preferably 0.005 to 95% by weight of the active substance
  • the active substances according to the invention can be used in the preparations as a mixture with other active compounds, e.g. Fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth factors, plant nutrients and agents to improve the soil structure are present.
  • active compounds e.g. Fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth factors, plant nutrients and agents to improve the soil structure are present.
  • the active ingredients can be used as such, as their formulations or as use forms, e.g. as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They can be applied in the usual way, for example by spraying, atomizing, dusting, scattering and watering.
  • the active substances can also be worked into the ground.
  • active substances in the various formulations mentioned or ready-to-use preparations is generally from 0.01 to 95% by weight, preferably 0.05 to 60% by weight.
  • the dosage or application rate of the active substance per unit area is generally 0.1 to 10 kg per ha, preferably 0.5 to 3 kg / ha. In special cases, however, it is possible or sometimes even necessary to apply an application rate outside the range mentioned above.
  • the invention further comprises a herbicidal composition which, as active substance, contains a compound according to the invention in admixture with a solid extender or carrier or in admixture with a liquid diluent or carrier which contains a surface-active agent.
  • the invention also encompasses a weed control method which is characterized in that a weed compound or its location is treated with a compound according to the invention alone or in the form of a preparation which, as an active ingredient, contains a compound according to the invention in admixture with a diluent or carrier , brings up.
  • the invention is further directed to crop plants which are protected against weed damage by being grown in areas in which a compound according to the invention, alone or in admixture with an extender, is grown immediately before and / or during the period of cultivation or development or carrier has been applied.
  • composition 100 parts in total
  • the amount of talc was changed according to the amount of the active ingredient and the total amount was hereby adjusted to 100 parts.
  • test field was plowed to a depth of 20 to 25 cm using a tractor using conventional rice cultivation methods. Immediately afterwards, water was poured from an irrigation channel into the field to one Height of 1 to 2 cm introduced and the first tillage (tilling) carried out. One or two days after the first soil treatment, water was introduced again to a height of about 5 cm and the last soil cultivation was carried out. Two days after the last soil treatment, the test field was divided into areas of 20 m 2 (2 mx 10 m) each using rigid plastic plates.
  • the rating "O" for the phytotoxicity for rice plants means lack of phytotoxicity.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP81102280A 1980-04-07 1981-03-26 Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide Withdrawn EP0037526A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4535280A JPS56140981A (en) 1980-04-07 1980-04-07 Substituted acetanilide compound, its preparation and herbicide containing the same as active constituent
JP45352/80 1980-04-07

Publications (1)

Publication Number Publication Date
EP0037526A1 true EP0037526A1 (de) 1981-10-14

Family

ID=12716878

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81102280A Withdrawn EP0037526A1 (de) 1980-04-07 1981-03-26 Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide

Country Status (7)

Country Link
EP (1) EP0037526A1 (enrdf_load_stackoverflow)
JP (1) JPS56140981A (enrdf_load_stackoverflow)
BR (1) BR8102089A (enrdf_load_stackoverflow)
DK (1) DK155581A (enrdf_load_stackoverflow)
ES (1) ES8201987A1 (enrdf_load_stackoverflow)
IL (1) IL62574A0 (enrdf_load_stackoverflow)
PT (1) PT72767B (enrdf_load_stackoverflow)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3038636A1 (de) * 1980-10-13 1982-05-27 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von substituierten oxyessigsaeureamiden
US4592774A (en) * 1983-12-22 1986-06-03 Union Carbide Corporation Herbicidal alpha heterocyclic carbinol carbamates, ureas and N-alpha-substituted acetylcarbamates
EP0348737A1 (de) 1988-06-27 1990-01-03 Bayer Ag Heteroaryloxyessigsäure-N-isopropylanilide
EP0373461A3 (en) * 1988-12-14 1990-10-10 Nihon Tokushu Noyaku Seizo K.K. Benzazoles
EP0537539A1 (de) * 1991-10-11 1993-04-21 Bayer Ag 2-(2-Benzoxazolyl-oxy)-acetamide und ihre Verwendung als Herbicides
US6544931B1 (en) 1999-07-20 2003-04-08 Bayer Aktiengesellschaft Substituted heteroaryloxyacetanilides and their use as herbicides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005501A2 (de) * 1978-05-20 1979-11-28 Bayer Ag Heteroaryl-oxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005501A2 (de) * 1978-05-20 1979-11-28 Bayer Ag Heteroaryl-oxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3038636A1 (de) * 1980-10-13 1982-05-27 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von substituierten oxyessigsaeureamiden
US4592774A (en) * 1983-12-22 1986-06-03 Union Carbide Corporation Herbicidal alpha heterocyclic carbinol carbamates, ureas and N-alpha-substituted acetylcarbamates
EP0348737A1 (de) 1988-06-27 1990-01-03 Bayer Ag Heteroaryloxyessigsäure-N-isopropylanilide
US4968342A (en) * 1988-06-27 1990-11-06 Bayer Aktiengesellschaft Herbicidal N-isopropylheteroaryloxyacetanilides
EP0373461A3 (en) * 1988-12-14 1990-10-10 Nihon Tokushu Noyaku Seizo K.K. Benzazoles
EP0537539A1 (de) * 1991-10-11 1993-04-21 Bayer Ag 2-(2-Benzoxazolyl-oxy)-acetamide und ihre Verwendung als Herbicides
US5328897A (en) * 1991-10-11 1994-07-12 Bayer Aktiengesellschaft Herbicidal 2-(2-benzoxazolyl-oxy)-acetamides
US6544931B1 (en) 1999-07-20 2003-04-08 Bayer Aktiengesellschaft Substituted heteroaryloxyacetanilides and their use as herbicides

Also Published As

Publication number Publication date
JPS56140981A (en) 1981-11-04
PT72767B (en) 1982-03-23
PT72767A (en) 1981-04-01
JPS6314711B2 (enrdf_load_stackoverflow) 1988-04-01
ES501109A0 (es) 1982-01-16
BR8102089A (pt) 1981-10-13
DK155581A (da) 1981-10-08
IL62574A0 (en) 1981-06-29
ES8201987A1 (es) 1982-01-16

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Inventor name: AYA, MASAHIRO